Preparation of chiral C5-building blocks for terpene synthesis by bakers' yeast reduction of sulfur-functionalized prenyl derivatives

✍ Scribed by Toshio Sato; Kyoko Hanayama; Tamotsu Fujisawa

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 278 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)86710-6

✦ Synopsis

Enantioselective hydrogenation of several a,% -unsaturated aldehydes and allylic alcohols of sulfur-functionalized prenyl derivatives with bakers' yeast gave bifunctional chiral (S)-and (R)-es-building blocks for terpene synthesis with high enantiomeric excess.

Microorganism-or purified enzyme-mediated reactions of synthetic substrates provide a useful method for preparing chiral building blocks in natural product synthesis.' Of the microorganisms so far used, Saccharomyces cereaisiae (bakers' yeast) has been widely employed for the asymmetric reduction of car-bony1 compounds to prepare the corresponding chiral secondary alcohols.' Although bakers' yeast is effectively used in reduction of variety of carbonyl compounds, it can also enantioselectively reduce carbon-carbon double bond in limited kinds of a,8-unsaturated carbonyl compounds,3~7 allylic alcohols,' and nitroalkenes.' Recently, we have demonstrated that introduction of sulfur